Methanol → 4-Methyl hydrogen D-aspartate hydrochloride

HRID 651329

Reaction equation

HRID 651329 reaction equation
[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5].S(Cl)([Cl:12])=O.[CH3:14]O>C(OCC)C>[CH3:14][O:5][C:4]([CH2:3][C@@H:2]([NH2:1])[C:7]([OH:9])=[O:8])=[O:6].[ClH:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 83887D-Aspartic Acid

Product 1

HCID 568281834-Methyl hydrogen D-aspartate hydrochlorideYield 78%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of D-aspartic acid (10.0 g, 75.1 mmol) in 50 mL methanol is treated with thionyl chloride (8.94 g, 75.1 mmol) at 0° C. The reaction mixture is stirred at 0° C. for 30 min, then at RT for 2 h. The resulting clear solution is diluted with 200 mL diethyl ether with rapid stirring. A white precipitate is formed which is collected by vacuum filtration, washed with diethyl ether and dried to yield 10.7 g (78%) of D-aspartic acid β-methyl ester hydrochloride.

Workup

  1. waitat RT for 2 h
  2. customA white precipitate is formed which
  3. filtrationis collected by vacuum filtration
  4. washwashed with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-5703d2ade3af4408a9da08641f6e1006
Source dataset
uspto-grants-2001_08
Patent number
US06277987B1

Linked notes

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